Serial entrepreneurs have plenty to tell you, but they also have to breathe, and you should take such moments as opportunities to contribute to the conversation. Say the wrong thing and lose their respect forever.
Do say: “Well, the landscape is always shifting.”
Don’t say: “Doesn’t that app already exist?”
Do say: “Oftentimes, it’s the moves you don’t make that end up being more important than the strategies you actually implement.”
Don’t say: “Were your parents weird about lending you the money, or did they pretend it was a really good investment?”
Do say: “I guess I’d say I’m fiscally conservative, but I’m socially liberal.”
Don’t say: “It sounds like you have no clear values and your politics are rooted entirely in self-interest.”
Do say: “That’s the beauty of the gig economy—it gives you the autonomy to make decisions that best suit your goals.”
Don’t say: “The gig economy is just a way for corporations to exploit unprotected workers and suggests that every possible interaction in life involves a transaction.”
Do say: “That’s really interesting.”
Don’t say: “Can we talk about something else?”
Do say: “Yeah, I’ve definitely been keeping an eye on V.R. That’s a sector on the verge of a breakout moment.”
Don’t say: “Can you please stop vaping in my face?”
Do say: “Imagine Dragons are very cool.”
Don’t say: “Imagine Dragons are not cool.”
Do say: “With all the negativity in the world these days, conscious capitalism is more important than ever.”
Don’t say: “Sure, ‘conscious capitalism’ sounds great. What do you think about ‘dry water’ and ‘cold fire’?
Do say: “Cross-platform collaboration is tricky because you can never be sure which technologies will adapt with the market and which will become antiquated.”
Don’t say: “It’s almost like a parlor trick that you’re able to just keep talking and talking without even stumbling into saying something interesting.”
Do say: “That kind of innovation is going to change the world.”
Don’t say: “Your job is literally nonsense.”
Do say: “Uber, but for açaí bowls.”
Don’t say: “Public libraries, but shinier and without books and privatized in order to convince young people that the resources they need to become self-starters are membership programs you can purchase rather than privileges inherent to our flawed society and also wow I hate to admit it but this açaí bowl really was worth sixteen dollars.”
